Sodium Iodide → Ethyl 5-(4-chloro-2-formyl-3-methoxyphenoxy)pentanoate

HRID 485166Notes

Reaction equation

HRID 485166 reaction equation
[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].Br[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH:5]=[O:6])[C:3]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 202715353-Chloro-6-hydroxy-2-methoxybenzaldehyde

Product 1

HCID 20271542Ethyl 5-(4-chloro-2-formyl-3-methoxyphenoxy)pentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloro-6-hydroxy-2-methoxybenzaldehyde (1.9 g, 0.0102 M), ethyl 5-bromopentanoate (2.13 g. 0.0102 M), anhydrous potassium carbonate (1.55 g), sodium iodide (56 mg), and 95% ethanol (25 ml) were refluxed with stirring (17 hr). The cooled reaction mixture was filtered and the solid washed well with ethanol. The filtrate was evaporated to dryness and the residue partitioned between ether and water. The organic layer was separated and washed with 2 N sodium hydroxide solution, water, dried (magnesium sulphate) and evaporated to give ethyl 5-(4-chloro-2-formyl-3-methoxyphenoxy)pentanoate as an oil.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe solid washed well with ethanol
  4. customThe filtrate was evaporated to dryness
  5. customthe residue partitioned between ether and water
  6. customThe organic layer was separated
  7. washwashed with 2 N sodium hydroxide solution, water
  8. dry with materialdried (magnesium sulphate)
  9. customevaporated

Sources & evidence

ORD record
ord-279b22c350924e0f954f4db6d50fd75e
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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